Water → HCID 53784545, compound

HRID 247675Notes

Reaction equation

HRID 247675 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([CH:38]=O)=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)#[N:25].O>COC(C)(C)C.O1CCCC1.C(OCC)(=O)C>[CH3:2][O:3][CH:4]=[CH:38][C:35]1[CH:34]=[CH:33][C:32]([C:29]2[CH:28]=[CH:27][C:26]([C:24]#[N:25])=[CH:31][CH:30]=2)=[CH:37][CH:36]=1

Participants

7

Reactant 3

HCID 962WaterHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 27592144'-Formyl-biphenyl-4-carbonitrile

Product 1

HCID 53784545HCID 53784545, compoundYield 91.6%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 12.4 g of methoxymethyl-triphenylphosphonium chloride in 120 ml of t-butyl methyl ether was treated within 3 minutes with 4.1 g of potassium t-butylate while gassing with argon at 0° C. and the mixture was stirred for a further 1 hour at 0° C. Thereafter, the mixture was treated within 10 minutes with a solution of 5.0 g of 4'-cyano-4-biphenylcarboxaldehyde in 40 ml of tetrahydrofuran and the resulting mixture was stirred for a further 1.5 hours at room temperature. The reaction mixture was subsequently poured into 200 ml of water and extracted three times with 150 ml of diethyl ether each time. The organic phases were washed twice with 150 ml of water each time, dried over magnesium sulphate and concentrated. The residue obtained was dissolved in 25 ml of ethyl acetate and the solution was treated with 350 ml of petroleum ether. After leaving to stand for 10 minutes at -20° C. the precipitated triphenylphosphine oxide was filtered off and the filtrate was concentrated to dryness. Low-pressure chromatography (0.5 bar) of the dark brown oil (9.5 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90) gave 5.2 g (91%) of 4'-(2-methoxyvinyl)-4-biphenylcarbonitrile as yellowish crystals; Rf-value (ethyl acetate/petroleum ether vol. 10:90) 0.17.

Workup

  1. customwhile gassing with argon at 0° C.
  2. stirringthe resulting mixture was stirred for a further 1.5 hours at room temperature
  3. extractionextracted three times with 150 ml of diethyl ether each time
  4. washThe organic phases were washed twice with 150 ml of water each time
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customAfter leaving
  9. waitto stand for 10 minutes at -20° C.
  10. filtrationthe precipitated triphenylphosphine oxide was filtered off
  11. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-09b6942d7e8d4468b7017bf52518004c
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Reaction notes

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